Aminodiarylsulfonpyrazolone azo dyestuffs



Patented Mar. 4, 1930- UNITED STATES PATENT OFFICE HUGO SCHWEITZER, OF WIESDORF, NEAR COLOGNE, AND WILHELM NEELMETER, OF

LEVERKUSEN, NEAR COLOGNE, GERMANY, ASSIGNORS T0 GENERAL ANILINE WORKS, INC., OF NEW YORK, Y., A CORPORATION OF DELAWARE .AMINODIARYLSULFONPYRAZOLONE AZO DYESTUFFS R0 Drawing. Original application filed January 5, 1926, Serial No. 79,476, and in Germany January 8, 192-5. Divided and this application filed March 30, 1927. Serial No. 179,708.

This invention relates to new azodyestufls prepared from the pyrazolonesof aminodiarylsulfones and their derivatives, such as sulfonic acids, carboxylic acids, hydroxy- 'carboxylic acids, etc; Such pyrazolones have not been used heretofore for the preparation of azodyestuifs.

lVe have found that the azodyestufis 0btainable from them have far superior fastness properties than those made from known pyrazolones.

They give yellow shades on wool which with respect to the properties of fastness to fulling, perspiration, and level dyeing, as well as unusual fastnss to light, are not obtainable with pyrazolone dyestuffs heretofore known. The same is true of their use as lake dyestuffs. In the latter case, one obtains yellow, water-soluble dyestuffs which are fast to lime and water when made up as distemper paints and which show an extraordinary fastness to light. These pyrazolones are also suitable as coupling components in the formation of chrome 'mordant dyestulfs phone-4-sulphonic acid.

for wool, especially those which contain an o-hydroxycarboxylic acid residue. With these products, one obtains wool dyestuffs.

which give very fast greenish yellows and also red tints that are fast to potting.

Example 1.327 parts by weight of 4- methyl 2 aminodiphenylsulp'hone 4 sulphonic acid are diazotized and coupled in the presence of sodiumacetate with 438 parts by weight of pyrazolone carboxylic acid obtained from 4'-methyl-2-aminodiphenylsul The dyestuif is salted out, isolatedand dried. It probably has the formula:

phonic acid. The reactions involved may be represented as follows:

moGsmOsonn-rmoi It is a colorless powder which dissolves easily in alkali and aqueous sodium acetate solution. It yields dyestuffs by coupling with diazo compounds.

If 4'-metliyl-2-aminodiphenylsulphone obtainable by reduction of the condensation product of 4-toluol-l-sulphonic acid and 2- nitro-1-chlorben-zol, is used in place of the 4 methyl 2 aminodiphenylsulphone 4 sulphonic acid, a dyestuif of similar characteristics is produced.

The methylpyrazolone obtained from 4- methyl-2-aminodiphenylsulphone is a colorless crystalline powder melting at 178180.

Example Q.327 parts by weight of 4- methyl-2-aminodiphenylsulphone-4-sulphonic acid are diazotized and coupled in the presence of sodium acetate with 438 parts by weight of thepyrazolone carboxylic acid obtained from f 4-methyl-4-aminodiphenylsulphone-2-sulphonic acid. The dyestufi' is ing in the free statethe formula:

salted out and worked up in the usual manner. It probably has the formula:

of the latter into th pyrazolone carboxylic acid by means of oxalacetic ester. It is a colorless powder which dissolves easily in alkali and aqueous sodium acetate solution and which yields dyestufi's by combining with" diazo compounds.

The products made. according to this iiivention are yellow to orange powders which 7 when dissolved in sulphuric acid give solutions of the same colors as their dyeings.

This application is a division of our application Serial No. 79,476, filed January 5, 1926. I t 4 We claim: 1. As new ing in the formula:

roducts, the azodyestufi's havee state most probably the wherein R represents an aromatic group and 1n which the benzene nuclei attached to the sulphone group may be substituted or not,

.which dyestuffs are obtainable by coupling a corresponding aromatic diazo compound with a pyrazolone carboxylic acid-of an amino-diarylsulphone.

2. As a new product, the azodyestufi haV- 4 01H HOOCG=N Nae-tam 3. As new products the azodyestuiis haV- ing in the free state mostprobably the formula:

wherein R represents an aromatic group, wherein the i substituent may be in either the 2- or 4-position to the nitrogen, and in which the benzene nuclei attached to the sulfone group may be substituted or not, which dyestufls are obtainable by coupling a corresponding arematic diazo compound with a pyrazolone carboxylic acid of an amino-diarylsulfone. 4. As new products, the azodyestufls having in the free state the formula:

in which R stands for an aromatic group,

in which the substituent may be either the 2- or 4-position to the nitrogen, and in which the benzene nucleus attached to the nitrogen may be further substituted.

5. As new products, the azodyestuifs having in the free state the formula:

in which R stands for an aromatic group, in.

which the substituent may be in either the 2- or 4-posi tion to the nitrogen.

6. As new products, the azodyestufi's having in the free state the formula:

in which each substituent may be in either the 2- or 4-p0sition to nitrogen and in which the benzene nuclei attached to the sulfone groups may be further substituted.

7 As new products, the azodyestufis having in the free state the formula:

I HO0CO=N 1 6 E i w N=N- H-CO H: wherein the benzene nucleus attached to the nitrogen on the right may be further substituted'and wherein the substituent on the right may be in either the 2- or 4-positi0n to the nitrogen.

8. As a new product, the azodyestufi having in the free state the formula:

substituent on the right may be in either the 2- or IE-position to the nitrogen.

In testimony whereof, We aifix our signatures.

HUGO SCHWEITZER. WILHELM NEELMEIER. 

